Cesium carbonate → HCID 86694357, compound

HRID 538927Notes

Reaction equation

HRID 538927 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:16]2[C@H:12]([N:13](S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[C:14](=[O:17])[O:15]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].C(N[C@H](C(O)=O)CS)(=O)C>CN(C=O)C>[Si:1]([O:8][C@H:9]1[C@H:16]2[C@H:12]([NH:13][C:14](=[O:17])[O:15]2)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12035N-Acetyl-L-CysteineHCID 86694358HCID 86694358, compound

Product 1

HCID 86694357HCID 86694357, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (3aR*,6R*,6aR*)-6-((tert-butyldimethylsilyl)oxy)-3-((2-nitrophenyl)sulfonyl)-hexahydro-2H-cyclopenta[d]oxazol-2-one (1.47 g, 3.32 mmol) and Cs2CO3 (2.164 g, 6.64 mmol) in DMF (25 mL) was added N-acetyl-L-cysteine (0.921 g, 5.65 mmol) and the reaction mixture was stirred for 16 h at RT. The reaction mixture was evaporated and the residue suspended in saturated NaHCO3 solution and extracted with EtOAc. Combined extracts were washed with brine, dried over MgSO4, filtered and concentrated. The title compound was obtained after purification by flash chromatography (heptane/EtOAc 90:10→50:50) as a yellow oil (0.84 g, 98%): TLC (heptane/EtOAc 1:1) Rf=0.28.

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with EtOAc
  3. washCombined extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-138270830dcf47aea5f6fb6e3cd907b5
Source dataset
uspto-grants-2014_10
Patent number
US08865894B2

Reaction notes

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